Development of functional group tolerant and room temperature hydrogen borrowing enolate alkylation reactions
<p>This thesis describes work completed to expand the scope of hydrogen borrowing enolate alkylation reactions. It was hypothesised that the development of a room temperature reaction would allow utility of a breadth of chemical space previously undemonstrated in these reactions at high temper...
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| Format: | Thesis |
| Language: | English |
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2023
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| Summary: | <p>This thesis describes work completed to expand the scope of hydrogen borrowing enolate alkylation reactions. It was hypothesised that the development of a room temperature reaction would allow utility of a breadth of chemical space previously undemonstrated in these reactions at high temperatures (80–180°C). The first strategy to achieve this was via the generation of excited state intermediates of the hydrogen borrowing cycle using visible light energy and a designed catalyst. A room temperature visible light driven reaction was realised and detailed mechanistic studies unveiled the role of visible light.</p>
<p>Later a light independent room temperature reaction was discovered and further developed to vastly expand the usable chemical space in hydrogen borrowing enolate alkylation reactions. A diverse range of nitrogen rich heterocycles were also demonstrated at higher temperatures (85°C) and mechanistic studies explained the need for anaerobic conditions in the reaction at room temperature.</p> |
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